Comedic genius Ben Stiller knows how to get away with just about anything, onscreen, even without shoes that make you look taller. After all, if you're 5'7” tall, and you can get away with portraying an international Supermodel, everybody notices the discrepancy, and doesn't care one bit. Paired with his buddy, Owen Wilson, who stands 5'10”, Stiller can make his lack of stature disappear by making you scream with laughter (and wearing elevator shoes).
In his breakout hit, There's Something About Mary, he was paired with the 5'9” actress Cameron Diaz, and made that difference work in his favor. Of course, there were some scenes in the movie where he sat on a taller seat than her, to distract the eye away from the height difference, and other scenes where she was barefoot and he was not. He made being the 'little guy' work, in a way that, perhaps, a taller man could not (like his costar Matt Dillon, who is 6'0”), and did not.
When filming Keeping the Faith with 5'10” costar Jenna Elfman, he explained that he got through the production with “shoe lifts and a sense of humor in bed”. If you're not as tall as your costar or companion, perhaps you can take a page from Mr. Stiller's book, and use a sense of humor to get past the difference in height. Add to that a great pair of shoes that make you taller, and you'll be ready for just about anything, including a photo op with an NBA star. In that case, make sure you take advantage of a good camera angle, a comic sight gag, and the fact that professional basketball players make just about everyone else look short.